Enterprising Investor
Practical analysis for investment professionals

Leadership, Management & Communication Skills


Where AI Ends and Investment Judgment Begins

AI’s growing capabilities challenge traditional investment skill, shifting competitive advantage toward governance, process, and judgment.

AI Strategy After the LLM Boom: Maintain Sovereignty, Avoid Capture

Yann LeCun’s testimony reframed for investment leaders: why AI sovereignty, platform control, and LLM economics shape organizational risk.

Keynesian Folly: Why AI Will Never Fully Automate Finance

AI automates tasks in finance and boosts efficiency, but reflexive markets ensure interpretation and oversight remain irreducibly human work.

Defined Contribution Top Trends for 2026: What Plan Sponsors Need to Get Right

Key trends shaping US defined contribution plans in 2026, from technology and education to investment strategy, regulation, and plan design decisions.

AI in Finance: Changing Workflows, Growing Demand for Human Judgment

GenAI is transforming investment workflows, raising critical questions about human judgment, task design, and the future of the profession.

Managing Client Fear: The Cognitive Skill Every Financial Advisor Should Master

A simple cognitive trick helps advisors reframe client fear, restore perspective, and guide decisions grounded in long-term goals.

From Risk to Resilience: What Finance Can Learn from the Futures

From forecasting to foresight: how scenario thinking enhances risk awareness and long-term resilience in finance.

Design Beats Luck: How AI Taxonomy Can Help Investment Firms Evolve

Without an AI taxonomy, investment firms risk overrelying on agentic AI and underutilizing it for optimal capital allocation.

Why Financial Advisors Struggle to Embrace Bitcoin’s Rise

Bitcoin challenges financial orthodoxy, valuation models, and regulation, forcing professionals to rethink what money and value really mean.

AI Can Pass the CFA® Exam, But It Cannot Replace Analysts

AI’s CFA exam success underscores finance’s next frontier: mastering technology while keeping human judgment at the core.